3-diethylaminomethylpyridine salt of penicillin



Patented Oct. 6, 1953 UNITED STATES PATENT OFFICE 3-DIETHYLAMIN OMETHY LPYRIDIN E SALT OF PEN ICILLIN Harley W. Rhodehamel, Jr., Indianapolis, Ind., assignor to Eli Lilly and Company, Indianapolis, Ind., a corporation of Indiana N Drawing. Application February 13, 1952, Serial No. 271,441

2 Claims. (Cl. 260239.1)

1 2 This invention relates to a novel penicillin salt sium salt of pencillin G in 1.8 ml. of water is and the preparation thereof. added a solution of 0.3 g. of 3-diethylamino- I have discovered that 3-diethylaminom'ethylmethylpyridine hydrochloride in 5 ml. of water. pyridine or its salts can be combined with peni- The mixture is cooled and stirred occasionally cillin or its salts by neutralization or metathetical 5 whereupon the slightly soluble 3-diethylaminoreactions to form a sparingly soluble penicillin methylpyridine salt of penicillin G precipitates. salt, thereby affording a means of precipitating The salt is separated, and dried in vacuo. penicillin from solution, and of purifying peni- 3-diethylaminomethylpyridine can be prepared cillin. Moreover, the novel penicillin salt can be by the desulfurization of N ,N-diethylthionicotinutilized therapeutically. A prolonged penicillin amide as reported by Kornfeld, J. Organic Chem. blood level can be secured upon administering the 16, 131, (1951).

salt parenterally by methods known to the medi- I claim: cal art. 1. The 3-diethylaminomethylpyridine salt of The following examples illustrate the preparapenicillin represented by the following formula in tion of the novel salt of this invention: which P represents penicillin:

Example 1 02115 To a solution of 2 g. of penicillin (e. g. a commercial mixture of the several penicillins) dissolved in 25 ml. of amyl acetate are added 2 g. of 3-diethylaminomethylpyridine dissolved in 30 ml. \N

of amyl acetate. The mixture is cooled and stirred occasionally whereupon the 3-diethylami- The 3'd1ethylammomethylpyndme salt of nomethylpyridine salt of penicillin precipitates. penicillin The salt is isolated as by decantation or filtration, HARLEY W. RHODEHAMEL, JR. and dried in vacuo.

The salt is represented by the following References Cited in the file of this patent mula in which P represents penicillin:

UNITED STATES PATENTS Number Name Date 5 2,569,666 Granatek Oct. 2, 1951 N 2,578,651 Buckwalter Dec. 18. 1951 E Z 2 FOREIGN PATENTS e Number Country Date To an aqueous solution of 0.3 g. of the potas- 645.037 Great Britain Oct. 25. 1950 

1. THE 3-DIETHYLAMINOMETHYLPYRIDINE SALT OF PENICILLIN REPRESENTED BY THE FOLLOWING FORMULA IN WHICH P REPRESENTS PENICILLIN: 